Pyridylethylation of some 4-azolidones

Lazovskaya, M. A.; Baranov, S. N.; Sheinkman, A. K.; Rok, A. A.

doi:10.1007/bf00945490

Cited by 3 publications

(6 citation statements)

References 2 publications

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“…Similarly, 2,4-thiazolidinediones react with equimolar amounts of 4or 2-vinylpyridines to form AT-[/3-(2-or 4-pyridyl)ethyl]thiazolidine-2,4-diones218 (218,219).…”

Section: -(4-ethoxyphenyl)imino-3-(4-ethoxyphenyl)-4-thia-mentioning

confidence: 99%

Chemistry and biological activity of thiazolidinones

Singh¹,

Parmar²,

Raman³

et al. 1981

Chem. Rev.

398

183

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“…Similarly, 2,4-thiazolidinediones react with equimolar amounts of 4or 2-vinylpyridines to form AT-[/3-(2-or 4-pyridyl)ethyl]thiazolidine-2,4-diones218 (218,219).…”

Section: -(4-ethoxyphenyl)imino-3-(4-ethoxyphenyl)-4-thia-mentioning

confidence: 99%

Chemistry and biological activity of thiazolidinones

Singh¹,

Parmar²,

Raman³

et al. 1981

Chem. Rev.

398

183

View full text Add to dashboard Cite

“…With the possibility of an undesired elimination reaction in mind, we decided that instead of attempting to suppress the elimination reaction itself, that it would be more prudent to explore the feasibility of a Michael addition of thiazolidine-2,4-dione to an acrylate. There are numerous examples of aza-Michael addition to conjugated esters and similar compounds in the literature. , However, aza-Michael additions of thiazolidine-2,4-dione compounds were scarce, and we were only able to find a few examples of aza-Michael additions of thiazolidine-2,4-dione containing compounds to electron deficient alkenes. , …”

Section: Resultsmentioning

confidence: 84%

“…3,4 However, aza-Michael additions of thiazolidine-2,4-dione compounds were scarce, and we were only able to find a few examples of aza-Michael additions of thiazolidine-2,4-dione containing compounds to electron deficient alkenes. 5,15 In our initial survey of aza-Michael reactions to ester and ketone derived Michael acceptors, work reported by the Kim group using DBU as a catalyst and work reported by the Xia group using phosphine compounds as catalysts caught our eye. 3 We hoped that similar conditions would allow for successful aza-Michael addition of thiazolidine-2,4-dione to acrylates and similar electron deficient alkenes.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Development of a DABCO-Succinic Acid Based Catalytic System for the Aza-Michael Addition and Aza-Michael/Knoevenagel Tandem Reaction of Thiazolidine-2,4-dione to Electron Deficient Alkenes

et al. 2021

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A DABCO catalyzed aza-Michael addition of thiazolidine-2,4-dione to a variety of electron deficient alkenes has been developed. Additionally, a DABCO/succinic acid salt system has been designed that allows for the one pot tandem aza-Michael/Knoevenagel reaction of thiazolidine-2,4-dione to give difunctionalized thiazolidine-2,4-dione products. To the best of our knowledge, this is the first example of a one-pot tandem aza-Michael/Knoevenagel reaction involving thiazolidine-2,4-dione.

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“…The 2‐vinylpyridine motif 255 reacts with thiazolidinedione forming 3‐(2‐(pyridin‐2‐yl)ethyl)thiazolidine‐2,4‐dione 256 (Scheme 86). [284] …”

Section: Reactivity Of 24‐thiazolidinedionementioning

confidence: 99%

Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

et al. 2023

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Thiazolidinedione (TZD) is one of the privileged heterocyclic rings and has shown many biological applications in medicinal chemistry and drug discovery. This review covers the synthetic approaches of TZD and its derivatives, different synthetic techniques for affording the desired regioselectivity and stereoselectivity, and the techniques that would enhance reaction conditions such as microwave, one‐pot, or ultrasound synthesis. It focuses on synthetic challenges of glitazones and the transformation of other heterocycles to TZD. Moreover, the chemical and biological behavior of TZD through the substitution in the N3 position, modification of the C5 position, annealing in complex heterocyclic systems, and hybridization with other pharmacologically attractive moieties are discussed. All reactions mentioned are provided as possible with different reaction conditions, mechanisms, derivatives scope, yield and clarified by applications of such reactions in the construction of potential medicinal agents. The review also answers questions about rapid racemization of glitazones, their toxicity, considering TZD as pan‐assay interference compounds (PAINS) or not, and the influence of saturation of 5‐position of TZD in their biological activities. This review is a comprehensive guide to make informed decisions for construction of TZD derivatives with biological potentials.

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Pyridylethylation of some 4-azolidones

Cited by 3 publications

References 2 publications

Chemistry and biological activity of thiazolidinones

Chemistry and biological activity of thiazolidinones

Development of a DABCO-Succinic Acid Based Catalytic System for the Aza-Michael Addition and Aza-Michael/Knoevenagel Tandem Reaction of Thiazolidine-2,4-dione to Electron Deficient Alkenes

Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

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